How to Actually Cross Things Off Your Bucket List in 2017

As I type these words I’m currently sitting on a Singapore Air Suites Class flight that retails for $10,455.

Yes, you read that price right.

Hold on one second, let me take a photo:

Not a bad office for the day.

Any moment now, my appetizer course is due to arrive which is made up of lobster, caviar, and is served with a side of Vodka.

When asked if I wanted Krug or Dom Perignon after boarding, I did what any sensible person would do: I asked for a glass of each. Then I washed it down with a glass of Blue Label.

At first I preferred the Krug, but as the flight went on found myself switching to the Dom.

And I still have 15 hours of fly time left.

Over the last 7 years the number of bucket list experiences I’ve ticked off has increasingly gone up.

Before this flight I had a personalized tour of the island of Islay in Scotland where I was treated to some of the most rare whiskey on Earth.

A private tasting at the Ardbeg Distillery on Islay.

I played some of the most exclusive golf clubs in the world, and also played the most famous of them all, The Old Course at St. Andrews.

Finally playing the most famous golf course in the world: The Old Course at St. Andrews

And now here I am on the most indulgent and lavish flight I could ever have imagined.

But why brag about this?

To make a point.

I’m no different than anyone else, but there’s one thing I’ve done repeatedly that has led to such amazing experiences, and that’s what we’re going to talk about in today’s post.

In this post you’re going to learn my biggest secret for actually accomplishing things on your bucket list in 2017, and other tips for showing you how to do more cool stuff in life.

How to Actually Cross Items Off Your Bucket List in 2017

About two months ago I realized I’d have to book a flight from Bangkok to Portland after traveling for a month on a round-the-world trip.

Naturally I started looking at my airline miles to see what the options were, and decided I wanted to try and do something, well, memorable.

A Suites Class flight on Singapore Air is one of the most sought after tickets in the world, and despite the astronomically high retail price ($10,455 to be exact), the experience can be downright affordable with the help of airline miles.

So I began telling people I wanted to take a Suites Class flight.

I talked all about the wonders of travel hacking, and how cool it would be to have your own little compartment with doors you could close.

I talked about it more than I probably should have, but by doing so it allowed me to do one very important thing: actually book the ticket.

And that’s the secret.

The more I talk about and joke about the big things I want to do, the more they actually come true.

Getting Custom Wedding Suits Made in Vietnam

For two years my wife Tate and I joked about what a cool story it would be if we flew to Saigon to get custom suits made for my groomsmen for our wedding.

18 months later I’m flying from Orlando to Hong Kong to meet her on a work trip before proceeding to Vietnam for a week.

Final price? Less than $100 a suit.

Getting fitted for my wedding suit in Vietnam

Playing the World’s Best Golf Courses

A couple years ago, I started telling people I wanted to play the top 100 golf courses in the world, and at the time I’d played exactly…zero.

My friend Ryan and I in Krabi, Thailand about a week after I arrived in Thailand.

Smoking Cigars in Cuba

Back while I was in my day job I made a bucket list goal of wanting to go to Cuba before the embargo was lifted and smoke a cigar.

This one I truly thought would never happen.

After planning a trip to Mexico three years later, I told a couple of the guys I was going with I thought it’d be cool to go to Cuba. A day later Clay was looking up flights and insisting we make it happen.

Derek and I with our buddy Clay at Hotel Ambos Mundos in Havana, Cuba.

Why This Bucket List Strategy Works

Ok, that was a nice trip down memory lane for me, but why exactly does this work?

In each case, I firmly believe the reason that things actually came together was just because I talked (a lot)about doing them.

I’ve found that the more I talk about something, even if it begins as a joke, like our suits in Vietnam idea, the more it slowly gets engrained in your head that it could be real.

It’s kind of like in Napoleon Hill’s “Think and Grow Rich,” where he tells you to say words of affirmation in the mirror everyday like “I will be wealthy” , without being quite as deliberate, and well, weird about it.

I think my dad thought I was crazy when I first mentioned the Suites class ticket, and he rolled his eyes a bit like it would never happen.

I just called him from The Private Room in SIN while drinking a Blanc Des Millienaires 1995, to let him know I was about to board.

The brain is a powerful thing, and the more you talk about something, the more it will subconsciously look for opportunities to help you make your outlandish ideas a reality.

Other Tips for Crossing Off Bucket List Items

While I firmly believe the absolute best way to continually have once in a lifetime experiences in your life is to tell people about your plans, no matter how crazy they may seem, there’s a number of other things I’ve done that have helped make so many of these crazy stories a reality.

Let’s look at a few of them.

1) Create Your Bucket List. Duh.

Here’s the thing, if you don’t have ideas of what you want to do in life, you’re probably not going to do much.

Or you may have a passing idea, but if you don’t document what that is, there’s a good chance you’ll put it off and forget all about it.

Spend $5,000 in the first 3 months. (If this seems difficult, it’s actually much easier than you might think with a few strategies) Note: I actually used Amex Platinum points for this particular redemption, but the Sapphire gives you more flexible points and a more widely available bonus

My top 100 quest would be much more difficult (and expensive) without it.

Sidenote: I’ve never had such attentive and friendly service in my life. The flight attendant just insisted she take my photo in just about every imaginable spot on the plane. You could tell, she’s done this before.

Writing this post at 37,000 feet.

3) Start a Lifestyle Business

Do you think if I were still working 50 hour weeks in finance I’d have the freedom and the flexibility to have all of these experiences?

Maybe, but it’d be much more difficult.

If it weren’t for building my business and this website, I’d most likely only have been able to do a small fraction of the things I’ve done in the last 7 years.

It’s opened doors in a similar way to Breaking Eighty, just take this trip to Jordan as an example.

But, by allowing myself the ability to work anytime and from anywhere, I’m able to leverage opportunities on a more regular basis.

5) Set Goals and a Timeline

This is something that so often gets overlooked. When I first created my bucket list, I had a goal of crossing off on average of one thing a month. I have similar goal, of at least 12 golf courses a year.

Think about a timeline that is reasonable, yet is also uncomfortable enough to get you to take action.

Bucket List: Accomplished

I recognize that this lifestyle I have is a privilege. It’s something I’ve worked hard to achieve, but it’s also something than can disappear in the blink of an eye, so I do my best not to take it for granted.

Sean i’d love to hear more about how you went about starting your golf site.

Specifically: -Did you start it with a plan in mind? IE-Get ‘X’ followers, promote courses for players and target certain products/clients to get comps or ambassadorship? -When you started what was key in driving traffic? -Did you start with an avatar of who you wanted to speak to or did you plan on being open to as many as possible?

1) My plan for the first year was to not worry about money, and just create the golf site that I wanted to read. That meant honest reviews, pretty photos, and cool writeups of some of the best courses around.

2) I had three main goals when I first launched it: meet cool people in the industry, potentially get free golf, and get access to some of the courses and clubs I wouldn’t have been able to experience otherwise.

3) Search has been the biggest long term driver of traffic. The site ranks very well, and for almost every review I do, I’ll end up ranking for my main key terms.

4) I kept it totally open and tried not to have too many expections. This allowed me to be fluid, not make assumptions, and adapt based on the responses I was seeing.

For instance I thought the course reviews would be the biggest driver of search traffic. In reality it’s been product reviews.

On social its been the opposite though. No one cares about the products, but they LOVE the course photos.

By not having too many rigid assumptions at first, I’ve been able to adapt to that reality.

I’m 100% with you. I started talking about moving to Mexico for 6 months about a year ago, but couldn’t go until after my son’s wedding. I left 4 days later and am now living and working from my window overlooking the beautiful Spanish Colonial town of San Miguel de Allende. It was through talking about it that I pushed myself to make it happen.

Now I’d love to know more about hacking airfares. I have friends in Thailand who will only be there another 8 months and I want to go visit!

Absolutely Sean. My husband and I have been setting goals and voicing them for years. Guess what? We now have 130 countries we’ve visited and travelled for 11 out of the last 20 years. Funnily enough, FB sent me a memory yesterday. It was from October 2012. We had just met an Aussie woman in Turkey who had just finished a sailing trip in the Med. She told us the Captain was moving to The Caribbean. I posted on FB that day that I thought we had found a way to see the Caribbean – great value and great adventure. Well…We started our dream trip, learning how to sail as crew, on that very same yacht last November. We spent 4 months cruising the Caribbean for a fraction of the cost of a charter trip. What an adventure! I wonder if it would have happened if we hadn’t made that very visible commitment. Right now we’re telling anyone who wants to listen about our plans to cycle for 12 to 18 months in North America. It would be a brave man who would bet that it won’t happen.

Sharyn, now THAT is a cool story!! When I first started this site back in 2009 I was SO set on heading to the Caribbean to learn to sail. I even had an opportunity, and asked me boss if I could take a 3 month sabbatical to go (that was a hard no lol).

It all sounds great, but the inner sceptic in me is floating to the surface and trying to decode if this isn’t some elaborate scam to part me with my money or really a useful tool on the journey to establish an earning business with bucket list benefits.

Will continue to digest and decipher. At the worst I’m reading some fun posts.

Great post Sean! Good to see a Portland boy make good and wow… what a flight! I have been feeling in a bit of a funk lately and saw my, generally glass half full, mindset turning to the fears instead. Thanks for the inspiration to get back on track.

Your post inspired me to draft one of my own announcing a project I’ve been thinking about for a long time.

I don’t think I’ll release that post until next year, but it was a great feeling to lay out the entire idea, even if only strictly as an announcement of something I’ve had on my bucket list for more than two decades.

I have mentioned it to my friends and do think that this has lead to thinking about it more frequently and at a deeper level. Plus, it primes my attention for actually seeing the opportunities to realize it right in front of me all the time. Thinking about it even made a book leap out of a bookstore shelf that has been a great help in thinking about it so far.

The weird think about it, however … is that it’s a brick and mortar business idea. Yes, sacrilege, but after 4 years as a digital nomad, I’m seriously thinking of …

… making an announcement and sharing my idea. It’s totally tied to my current online business, but with an interesting twist. And if I’m going to pull it off, I’ll need all the help I can get. So the sooner I get talking about it, the better.

Maybe I won’t wait until next year to put this post out there after all …

Anyhow, thanks! I like posts like these that get me to write my own in response. I’ve already mentioned this post of yours in my draft. I’ll link back and let you know when it goes live. 🙂

I’d love to know more about the point hacking you did for this particular flight. Do the 100k sapphire points transfer directly to Kris flyer? I saw on their upgrade chart that a business to suites upgrade from Singapore to US is about 70k points.

Also, can a Canadian get that sapphire card? I’m finding that travel hacking isn’t even really possible for a Canadian, at least not to the same extent, and we have to work 3x as hard to get even a quarter of the rewards Americans can get 🙁

Rachael, thanks for the comment! We’re going to be publishing a much bigger post on travel hacking in general, but let me try and answer your question.

Yes, the 100k can transfer directly to KrisFlyer at 1 to 1. As mentioned I actually transferred 92K Amex Points directly to KrisFlyer for this redemption – and I only did that becuase the amex points are harder to use than the ultimate rewards points.

Then when you book directly through KrisFlyer you get a 15% point discount. So the 107k saver fare from SIN to LAX was actually 91 and change.

I’m not sure about the upgrade, but I believe it was going to be 68k miles for the same routing in business class.

Long-time reader, first-time commenter here. This post really spoke to me, as the coming year promises to be a good one, and one where I will have more opportunity to cross some of those items off my bucket list (the one that I have yet to make!).